4-(Trifluoromethoxy)-1H-indole-2-carboxylic acid → HCID 53418161、化合物

HRID 2278653ノート

反応式

HRID 2278653 の反応式
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7](C(O)=O)[NH:8]2>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[F:17][C:2]([F:1])([F:16])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

参加物

4

反応物 1

HCID 167692654-(Trifluoromethoxy)-1H-indole-2-carboxylic acid

生成物 1

HCID 53418161HCID 53418161、化合物収率 40.2%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 7047Quinoline溶媒

反応条件

温度
200 °C

実験手順

0.18 g of copper(0) is added to a solution of 1.0 g of 4-(trifluoromethoxy)-1H-indole-2-carboxylic acid in 4.5 ml of quinoline under argon. The reaction mixture is heated at 200° C. for 5 hours, and is then cooled to ambient temperature. After dilution with 30 ml of diethyl ether, the mixture is filtered through Clarcel®. The filtrate is washed successively with 6×10 ml of a 6N hydrochloric acid solution, with 10 ml of a saturated sodium hydrogen carbonate solution and then with 10 ml of saturated brine. The organic phase is dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 25 g cartridge of 15-40 μm silica, elution being carried out with a 95/5 v/v cyclohexane/ethyl acetate mixture, at a flow rate of 20 ml/min. 0.33 g of 4-(Trifluoromethoxy)indole is thus obtained in the form of an amber oil, the characteristics of which are the following:

後処理

  1. temperatureis then cooled to ambient temperature
  2. filtrationAfter dilution with 30 ml of diethyl ether, the mixture is filtered through Clarcel®
  3. washThe filtrate is washed successively with 6×10 ml of a 6N hydrochloric acid solution, with 10 ml of a saturated sodium hydrogen carbonate solution
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue is purified by chromatography on a 25 g cartridge of 15-40 μm silica, elution

出典と根拠

ORDレコード
ord-afcb6154a16a4ed684cc02c7d8e666c7
出典データセット
uspto-grants-2015_09
特許番号
US09133168B2

反応ノート

読み込み中…